Cationic paint binders comprising the reaction product of substituted ureas, formaldehyde, and phenols

Abstract

Cationic paint binders obtained through reaction of substituted ureas with formaldehyde and phenols are described. The substituted ureas are obtained through reaction of an isocyanate compound carrying at least one free, and optionally also blocked, NCO-group with equivalent quantities of a secondary non-aromatic amine. After partial protonation, the binders are used in water-dilutable paints, particularly in cathodically depositable electrodeposition paints.

It is claimed: 
     
       1. A process for producing cationic paint binders water-dilutable on protonation comprising (A) reacting an isocyanate compound having at least one free NCO-group with a secondary non-aromatic amine to provide a substituted urea, the quantity of said amine utilized being equivalent to the said free isocyanate groups; and (B) condensing the substituted urea of (A) with formaldehyde and a phenol to form a condensate. 
     
     
       2. The process of claim 1 wherein the phenolic hydroxy groups of said condensate phenol are partially or totally etherified with epoxy compounds. 
     
     
       3. The process of claims 1 or 2 wherein said isocyanate compound in addition to said free isocyanate group carries blocked NCO-groups. 
     
     
       4. The process of claims 1, 2 or 3 wherein said secondary non-aromatic amine is an aliphatic amine. 
     
     
       5. The process of claim 4 wherein said aliphatic amine carries ketimine-blocked primary amino groups. 
     
     
       6. The process of claim 4 wherein said secondary aliphatic amine is a secondary alkanolamine. 
     
     
       7. The process of claim 6 wherein the secondary alkanolamine is the reaction product of monoalkyl- or monoalkanolamines with an epoxy compound. 
     
     
       8. The process of claim 6 wherein the secondary alkanolamine is the reaction product of acrylic acid esters with a primary amine substituted alkanediol. 
     
     
       9. The process of claim 6 wherein the secondary alkanolamine is the reaction product of diprimary diamines with monoepoxy compounds. 
     
     
       10. The process of claims 1, 2, 3 or 4 wherein the phenol in (B) is a phenol-aldehyde condensate carrying at least one formaldehyde-reactive site. 
     
     
       11. The process of claims 1, 2, 3 or 4 wherein the phenol in (B) is an aminoalkylation product of phenols carrying at least one formaldehyde-reactive site. 
     
     
       12. The process of claim 1 wherein the reaction product of the process has a titratable basicity corresponding to an amine value of at least 20 mg KOH/g. 
     
     
       13. The process of claim 12 wherein the amine value is at least 35 mg KOH/g. 
     
     
       14. A cathodically depositable electrodeposition paint comprising a binder produced according to claim 1. 
     
     
       15. Cationic paint binders water-dilutable on protonation comprising the condensation product of a substituted urea with formaldehyde and a phenol, wherein the substituted urea is the reaction product of an isocyanate compound having at least one free NCO-group with a secondary non-aromatic amine, the quantity of said amine utilized being equivalent to the said free isocyanate groups. 
     
     
       16. The cationic paint binder of claim 15 wherein the phenolic hydroxy groups of said condensation product are partially or totally etherified with epoxy compounds. 
     
     
       17. The cationic paint binder of claims 15 or 16 wherein said isocyanate compound in addition to said free isocyanate group carries blocked NCO-groups. 
     
     
       18. The cationic paint binder of claims 15, 16 or 17 wherein said secondary non-aromatic amine is an aliphatic amine. 
     
     
       19. The cationic paint binder of claim 18 wherein said aliphatic amine carries ketimine-blocked primary amino groups. 
     
     
       20. The cationic paint binder of claim 18 wherein said secondary aliphatic amine is a secondary alkanolamine. 
     
     
       21. The cationic paint binder of claim 20 wherein the secondary alkanolamine is the reaction product of monoalkyl- or monoalkanolamines with an epoxy compound. 
     
     
       22. The cationic paint binder of claim 20 wherein the secondary alkanolamine is the reaction product of acrylic acid esters with a primary amine substituted alkanediol. 
     
     
       23. The cationic paint binder of claim 20 wherein the secondary alkanolamine is the reaction product of diprimary diamines with monoepoxy compounds. 
     
     
       24. The cationic paint binder of claims 15, 16, 17 or 18 wherein the phenol is a phenol-aldehyde condensate carrying at least one formaldehyde-reactive site. 
     
     
       25. The cationic paint binder of claims 15, 16, 17 or 18 wherein the phenol is an aminoalkylation product of phenols carrying at least one formaldehyde-reactive site. 
     
     
       26. The cationic paint binder of claim 15 wherein the reaction product has a titratable basicity corresponding to an amine value of at least 20 mg KOH/g. 
     
     
       27. The cationic paint binder of claim 26 wherein the amine value is at least 35 mg KOH/g. 
     
     
       28. A cathodically depositable electrodeposition paint comprising the binder of claim 15.